This conversation tracks and critiques the human journey from the electronic frontier to the Anthropocene through the lens of the history of digital media. The first part of the conversation reveals complex trajectories between countercultures of the 1960s and their predecessors in the 1950s and 1940s. It links information technologies with historical struggles against totalitarianism, and inquires their contemporary potentials for creating a more tolerant society. The second part of the conversation analyses the main differences between the New Communalists and the New Left of the “Psychedelic Sixties.” Using the example of the Burning Man festival, it outlines trajectories of these movements into present and future of our consumerist society. The conversation explores the complex relationships between counterculture, cyberculture, and capitalism, and asks whether the age of informa- tion needs its own religion. Looking at mechanisms in which traditional inequalities have been reproduced in the communes of the 1960s, it touches upon contemporary Silicon Valley’s “soft discrimination.” The third part of the conversation explores contemporary transformations of various occupations. Looking at journalism, it shows that consequences of its transformation from watchdog of democracy into a tool of global neoliberalism are yet unclear, and seeks one possible solution in “computational journalism.” It also explores how the arts have often legitimated ideologies peddled by information technologies. Looking at human learning, it inquires the role of teachers in the contemporary society, and links it to the role of public intellectuals as writers of scholarly texts and builders of human networks. The last part of the conversation explores the main issues with cyber-knowledge. It examines traditional divisions between disciplines, and links them to cybernetics. It introduces the “biological metaphor” for describing the Internet and compares it to the traditional “computational metaphor.” It discusses the main pros and cons of Donna Haraway’s cyborg metaphor, and inquires whether the Internet needs to be treated differently from the rest of our infrastructure, such as electric grids and sewage systems. Finally, it briefly outlines the main contributions of counterculture and cyberculture to our understanding of human learning, and draws lessons from the age of ‘the endless frontier’ for the Anthropocene.